


The Winchester Brothers

by MidgardianMenace



Category: Supernatural
Genre: Blow Jobs, Cheating, Dean Winchester - Freeform, Doggy Style, F/M, Large Cock, Oral Sex, Reader-Insert, Rough Sex, Sam Winchester - Freeform, Sex, Smut, Vaginal Fingering
Language: English
Status: Completed
Published: 2017-10-09
Updated: 2017-10-09
Packaged: 2019-01-15 03:41:50
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,985
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12313056
Author URL: https://archiveofourown.org/users/MidgardianMenace/pseuds/MidgardianMenace
Summary: I was hiding something from them, a different secret from each. Each of them knew one of my secrets, each of themwasone of my secrets.





	The Winchester Brothers

 

The Winchester brothers. What can I say about Sam and Dean Winchester. That's what I get asked most, what are they like. The frequenter of this question is the thin, desperate, slutty, bimbos you find at trashy bars on Thursday nights, not that I'm judging or stereotyping in any way...  
They come to me, fantasies brewing in their minds of these two charming and handsome men being their saviours, sweeping them off their feet and taking them away from whatever little town they live in. They want to know all about them, what they're really like. I, being the kind hearted soul that I am, fulfill their fantasies by telling them exactly what they're like. Kind hearted, charming, sweet, caring men. The truth 100%. Then they go over to the boys and it becomes their job to let them down easy.   
That's what made me feel so bad about what I was doing. No, not about letting those girls believe for a moment that their knights in shining armour might have finally arrived, but about the secret I was keeping from the boys. That I was part of the reason they would never take those poor lonely girls away for the night. I was hiding something from them, a different secret from each. Each of them knew one of my secrets, each of them  _was_ one of my secrets. I made them promise not to tell the other what we were doing. If they ever found out...well, I don't know what might happen.   
Yep, you got me, I'm secretly sleeping with both brothers. I feel bad, I do, but it was addicting. Each one of them they're own brand of Winchester. They're so different. Sam likes to spoon, Dean likes to cuddle face to face. They almost switch personalities when your naked and alone with them. Sam likes it quick, he takes time to think through every other aspect of his life, so sex seems to be this release, this action of pure instinct. His brain shuts off and his motivation is pure pleasure. Dean likes to take his time, when he's on a hunt he's impulsive, he's always a shoot first ask questions later kind of guy, he knows what he wants and he gets it. Just the same as Sam though, when we're alone he feels differently. He acts like we have all the time in the world, he's slow and he's careful He feels every single moment, and revels in it. Either way I feel the adrenaline, the rush of not wanting the other to find out. When it first happened I meant to choose, to pick one and come clean about it, but I couldn't let either of them go.

 

~~~

 

I laid on my bed playing on my phone when there was a knock at the door. It opened slowly and Sam stood smiling at me.   
"Dean just went out" he spoke  
"Where?" I asked  
"Don't know, does it matter though?" He came in and shut the door behind him. I sat up and placed my phone on the nightstand  
"I guess not" I replied  
He laid down next to me on his side, and I rolled to face him. His lips were on mine in an instant, pushing against me. He darted his tongue out and I opened my mouth for him to explore. His hand found my face and brushed my hair away. Rolling on top of me he supported his weight on his elbow, deepening the kiss. Soon his hand trailed down my side and to my hip, holding it as he ground his hips into mine.   
"Ooo" he moaned into the kiss  
I reached between us and rubbed him through his jeans  
"Ya...ooo" his head fell to my shoulder  
I undid his jeans and he got them off with his underwear, laying back down on his back. His dick laid against his stomach. He put his hands behind his head, smiling as he looked from me to his long hard shaft.    
"Oh Sam" I smiled chuckling and placing myself between his legs "you're too funny"  
I blew on the tip and he closed his eyes. Wrapping my hand around him I slowly pumped him up and down. He threw his head back.   
"Please, come on" he whined chuckling at his own desperation  
"So desperate" I giggled licking my lips seductively   
I lowered my lips onto him. He let out a sigh and I watched him run his fingers through his hair. It was impossible to take all of his dick into my mouth, it was so long. So I used my hand to replicate thrusts near his base. One of his hands flung to his side and gripped the sheets firmly. Cupping his balls in my other hand I began kneading them the way I knew he liked.   
"Shit" he cursed at the sensation  
I was deep throating him as best as I could but I just couldn't fit him down.   
Finally I let his dick fall from my mouth with a pop. His eyes fluttered open, looking down at me. I crawled up his body and kissed him feverishly, hoping he would read how much I wanted him to touch me. I stood and slipped off the rest of my clothes to make sure it was obvious. Laying down beside him he ran his hand over one of my pert nipples, down my stomach, and along my wet slit. As he inserted three long fingers he bit gently on my earlobe.   
"Oooohh" I moaned softly  
His fingers moved back and forth slowly for a moment before he quickened the pace. I could feel how wet I was getting around his fingers and obviously he did too. He crawled on top of me and kissed me, his dick rubbing on my wet heat, his hair falling around his face. I couldn't help but tangle my fingers in it.  
"You ready for me?" He asked out of breath  
"Ya" I replied spreading my legs even more than they were  
He reached down and took his dick in his hand pushing it into me.   
"Mmm" I moaned  
He wasted no time in getting to quick, hard thrusts. He was so long he hit places I didn't even know existed and it made me moan.   
"Ya, like that" I gripped his shoulders, digging my nails into them  
It only spurred him on. He gripped my hip, holding me from bouncing to much. He pulled out for a moment and pushed back in. Once. Twice. A third time.  
"Uhhh" I cried as he pinched one of my nipples  
"Shit, I'm so close..." He moaned setting a relentlessly fast pace  
"Oh ya" I dug my fingernails into his skin and captured his lips  
"Shit. Shit. Shit" he cursed as I felt him cum inside me  
He reached for my clit as he rode out his orgasm and rubbed it roughly.   
"Uh, uh" I sighed as my core exploded and I erupted in waves of pleasure.  
He collapsed on top of me as I started to settle from my high. I raked my fingers through his hair a couple times, smiling, before he rolled off and pulled my back to his chest. He spooned me until we fell asleep, his snoring as loud as ever.

 

~~~

 

So many differences, how could I choose. It's like trying to decide if you like peanut butter more than jam, they're two completely different things. Cautious and impulsive, soft and hard, in check and in charge. They're vastly different, but one isn't better than the other. And let's not forget about the most important part. They were both well endowed. Sam had crazy length, while it didn't do much horizontally it did hit places that I would never have know we're there. Dean on the other hand was thick. The widest I'd ever seen. The amount of stretch when he entered me was delicious.

 

~~~

 

I was sitting on my bed with my phone in my hands when I glanced up from the screen. There in my doorway was Dean, casually leaning against the frame with his arms crossed  
"How long have you been standing there?" I asked smiling  
"Dunno" he replied casually  
"Ok" I chuckled "what's up?"  
"Nothin, Sam just left on his little trip"  
"Oh"  
He was gonna be gone overnight, something about visiting a friend from Stanford  
He casually walked into the room and sat next to me on my bed. I set my phone on the nightstand and turned around to face him. Pushing my hair off my shoulder he leaned in to press his lips to mine. I sighed at the feeling. His lips were so warm and inviting, as was his whole body. He was in his jeans and a white tshirt under an open army green button down with the sleeves rolled up. Despite the layers over his torso, I could feel the heat radiating off of his body. He hooked his arm around my waist and pulled me flush to his body. As our lips parted I looked up at him  
He smiled and shook his head a little.  
"What?" I asked smiling back at him  
"Nothin, just always amazed how easily I get lost in those eyes"  
I bit my lip and swung my leg over him to straddle his lap before pressing our lips together again. I wanted him closer, his lips were on mine, our chests were pressed together, and I still wanted him closer. I pulled away and held his face, just looking into his eyes.  
He pulled me back to his lips and kissed so gently, so intentionally, that it took my breath away.   
I pulled away and looked at him. Without breaking eye contact he flipped us over so he was on top of me, holding his weight on his elbow.   
He looked down at me with his eyebrows furrowed, like he was thinking "you are so beautiful"  
My breath hitched in my throat. He'd never been so passionate with me before. The way the words were falling from his lips, it was...different.   
We stared at each other intently   
"Dean..." I whispered  
He crashed his lips against mine letting his weight push me down a little more. The feeling of his warm body against mine was amazing, so comforting. I wrapped my arms around his neck, letting him know that I was more than happy with what he was doing. He took my bottom lip between his lips and nibbled it softly.   
"Mmm" I moaned opening my mouth  
His tongue darted between my lips to find mine. They tangled together in a heated battle. He tasted like mint from brushing his teeth and his warm breath fanned over my face from his nose.  
When we finally parted we were both breathing heavily. My hands were on his chest, and his free hand was tangled in my hair. He sat up and moved down my body. Lifting my oversized t-shirt just a bit he kissed my stomach just above my sweat shorts.   
"Mmm" I whispered looking down to him  
He looked up and caught my eyes, then pulled my shorts and underwear off. Settling between my legs he pushed my calves up onto his shoulders. He worked from the inside of my knee up my thigh with his mouth, kissing and licking.   
"Mmm, Dean" I sighed, a warmth forming in my stomach  
Finally his hot breath was on my core. He paused for a moment before he licked at my clit gently. My eyes rolled back and my hands found their way into his hair. His licking became deeper and longer, prodding his tongue into my hole.   
"Oh god, that feels so good" I moaned  
He placed his hands on my ass firmly and squeezed making my back arch off the bed. He pulled away and looked up at me and I smiled.   
"That's what I like to see" he crawled up my body and kissed me "I love that smile" he whispered  
I ran my hand down his toned chest and toyed with the waist of his jeans before I undid them, slipping my hand underneath them.  
"Ahhh" his forehead fell to my shoulder as I rubbed his hard cock through his underwear  
"Flip over" I whispered, biting his ear  
He rolled over and laid on his back and I was quickly on top of him. I pulled his zipper down and he helped me shed him of the rest of his clothes. My heart rate picked up at the sight of his thick cock. I wrapped my hand around it, but it didn't make it all the way around. I leaned over and ran my tongue across his slit  
"Fuuuuuck" he moaned  
I slipped his tip into my mouth and swirled my tongue around it, covering it with my saliva. I slowly took more of his length into my mouth, it pulled on my lips as I tried to take his whole shaft. I managed to get it in and so I hollowed my cheeks and began bobbing my head. My teeth scraped lightly against his cock as I pushed him down my throat.   
"Ooo. That's it princess, all the way in" he moaned  
His eyes were closed but he managed to get his fingers into my hair, urging me to go faster. I took a deep breath and pushed him in as far as I could, then bobbed my head in short strokes, constantly pushing him past the barrier of my mouth to my throat and pulling back.   
"Shit. Fuck. Fuck." He swore with each push back onto him  
"Christ" he was breathing heavily "you're gonna make me cum"  
I smiled in my head but he pulled me off of him. I looked at him pouting and he smiled.   
"Mm, that was amazing" he motioned for me to crawl up to him "but I want you"    
I bit my lip "I want you too"  
He grabbed my waist and flipped us over. I felt his warm cock between my legs, rubbing slightly. He sat up on his knees and brushed his tip against my core  
"Ahh, your so wet" he gripped my thigh  
"Dean" I gasped  
Slowly he pushed into me. He placed a hand on the bed beside my head and the other held my hip. The way his cock made my walls stretch was amazing. He felt so good inside me, so thick and warm. He filled me so full I could almost feel the pulse in his cock.   
"So tight, always so tight for me" he moaned through gritted teeth, staying still until I gave him the go ahead.   
I wrapped my legs around his waist and he took that as a sign to start moving, and God did he move. With every slow thrust I could feel my walls stretch. He pushed in and out and I felt my wetness begin to slide down my ass and drip on the bed.   
"Faster Dean" I begged  
"Whatever you say princess" he kissed my lips then balanced himself on his elbows, setting a new, ridiculous, speed. In and out and in and out. The sounds of our moans and slapping skin drowned out any other noise. My fingernails dug into the skin just below his neck on each shoulder. He groaned huskily. When he opened his eyes his pupils were almost completely black with lust. I started to rock my hips in time to get maximum penetration and it was driving me wild.   
"Dean" I cried  
"Ya baby" he replied in a daze  
"I...I...I'm gonna..." I had trouble forming words  
"I'm here" his voice was deep as he pressed his lips to mine "cum for me princess"  
"I...ahhhhhh" my body took over, convulsing around his thick cock "Uuuuhhhhhhhhhh" I moaned  
"Fuck!" Dean yelled as he gripped my shoulder and I felt his hot cum fill me up  
He thrust into me three more times as hard as he could before he collapsed on top of me. Our bodies were slick, our limbs were tangled, and our minds were mush. Our breathing was sporadic and shallow.   
He lifted an arm and rolled over "sorry"  
"No, I like being underneath you" I smiled  
He curled up on his side and I did the same, mirroring him. Our eyes were heavy as we looked at each other and he reached a hand to hold mine.   
He reached over to pull a blanket over him and then held one side open  
"C'mere princess" he whispered  
I shuffled over to him and buried my head in the crook of his neck. That's how we fell asleep.

 

~~~

 

I'd spent many days and nights thinking about my situation, thinking about Sam and Dean. This had gone on too long and I needed to end it, but how. I didn't want to loose them, either of them. I had made peace with the fact that once I tell one of them it may be over, both of them might want me gone. I was mad at myself for getting into this situation, this wasn't me. It just happened, and I was selfish because it felt good. The longer it happened, though, the more clear it became what I had to do. I had feelings for both the brothers, obviously, but in two very different ways. All of us were just hanging around the bucket and I knew it was time. I stood from my bed and looked myself over in the mirror. Sighing I left my room and walked down the hall. When I arrived in front of his door I stood there for a long while thinking about what I had to loose here, but I couldn't back down now. I slowly pushed the door open and found him on his bed. He smiled at me before I spoke.  
"Can we talk?"


End file.
